- GaCl3-Catalyzed C-H Cyanation of Indoles with N-Cyanosuccinimide
-
An efficient GaCl3-catalyzed direct cyanation of indoles and pyrroles using bench-stable electrophilic cyanating agent N-cyanosuccinimide was achieved and afforded 3-cyanoindoles and 2-cyanopyrroles in good yields and excellent regioselectivities. Notably, this protocol exhibited high reactivity for unprotected indoles and was applicable to a broad range of indole and pyrrole substrates.
- Wang, Xue,Makha, Mohamed,Chen, Shu-Wei,Zheng, Huaiji,Li, Yuehui
-
p. 6199 - 6206
(2019/05/24)
-
- Copper-Catalyzed Oxidative Dehydrogenative C(sp3)?H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources
-
A copper-catalyzed oxidative C(sp3)?H/N?H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp3)?N bond formation through a radical pathway generated by homolytic cleavage of di-tert-butyl peroxide and trapping of the radical(s) by copper catalysts. The reaction tolerates a series of functional groups, such as bromo, fluoro, ester, ketone, nitrile, methyl, and methoxy. free-NH-containing indoles, pyrroles, pyrazoles, indazoles, and benzotriazoles are successfully N-alkylated.
- Wang, Chang-Sheng,Wu, Xiao-Feng,Dixneuf, Pierre H.,Soulé, Jean-Fran?ois
-
p. 3075 - 3082
(2017/08/18)
-
- Aromatic heterocyclic compound and a method of producing aminonitrile
-
PROBLEM TO BE SOLVED: To provide a novel method of turning an aromatic heterocyclic compound into nitrile, by which a raw material having high toxicity is not needed, the amount of a byproduct can be reduced and structural restriction of a usage raw material is reduced.SOLUTION: In the method of turning the aromatic heterocyclic compound into the nitrile, a nitrogen-containing aromatic heterocyclic compound represented by general formula (1), a silicon compound represented by general formula (2) and a nitromethane are reacted in the presence of one or more zinc catalysts selected from the group consisting of zinc sulfonate, zinc sulfonamide and a zinc halide to obtain the nitrile compound of the aromatic heterocyclic compound represented by general formula (3).
- -
-
Paragraph 0083; 0084
(2017/06/02)
-
- Zinc-catalyzed direct cyanation of indoles and pyrroles: Nitromethane as a source of a cyano group
-
With nitromethane and diphenylsilane (Ph2SiH2), zinc triflate behaves as a Lewis acid catalyst for the cyanation of nitrogen-containing heteroarenes such as indoles and pyrroles. This is the first realization of the Lewis acid-catalyzed direct cyanation of a C(aryl)-H bond with no CN group-containing cyanating agent.
- Nagase, Yuta,Sugiyama, Tetsuya,Nomiyama, Shota,Yonekura, Kyohei,Tsuchimoto, Teruhisa
-
supporting information
p. 347 - 352
(2014/05/20)
-
- Practical one-pot transformation of electron-rich aromatics into aromatic nitriles with molecular iodine and aq NH3 using Vilsmeier-Haack reaction
-
Various electron-rich aromatics could be efficiently transformed into the corresponding aromatic nitriles in good to moderate yields by treatment with DMF and POCl3, followed by the reaction with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) in aq NH3. Some of less reactive aromatics, such as anisole, 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, and mesityrene, could be also transformed into the corresponding aromatic nitriles in good to moderate yields using N-methylformanilide and O(POCl 2)2, followed by the reaction with molecular iodine in aq NH3. Moreover, propiophenone derivatives could be successfully transformed into the corresponding β-chlorocinnamonitriles by the reaction with DMF and POCl3, followed by the reaction with molecular iodine and aq NH3. These reactions are novel metal-free one-pot methods for the preparation of aromatic nitriles from electron-rich aromatics and β-chlorocinnamonitriles from propiophenones.
- Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo
-
experimental part
p. 4588 - 4595
(2012/07/27)
-
- Lewis acid catalyzed direct cyanation of indoles and pyrroles with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS)
-
BF3?OEt2-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and pyrroles.
- Yang, Yang,Zhang, Yan,Wang, Jianbo
-
supporting information; experimental part
p. 5608 - 5611
(2011/12/03)
-
- Metal-free one-pot conversion of electron-rich aromatics into aromatic nitriles
-
Various electron-rich aromatics could be smoothly converted into the corresponding aromatic nitriles in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with molecular iodine in aqueous ammonia. The present reaction is a novel metal-free one-pot method for the preparation of aromatic nitriles from electron-rich aromatics.
- Ushijima, Sousuke,Togo, Hideo
-
experimental part
p. 1067 - 1070
(2010/06/14)
-